WO2005051103A1 - Produit alimentaire comprenant un extrait a base d'aiguilles de pin - Google Patents

Produit alimentaire comprenant un extrait a base d'aiguilles de pin Download PDF

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Publication number
WO2005051103A1
WO2005051103A1 PCT/GB2004/004575 GB2004004575W WO2005051103A1 WO 2005051103 A1 WO2005051103 A1 WO 2005051103A1 GB 2004004575 W GB2004004575 W GB 2004004575W WO 2005051103 A1 WO2005051103 A1 WO 2005051103A1
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WO
WIPO (PCT)
Prior art keywords
food product
product according
fat
oil
extract
Prior art date
Application number
PCT/GB2004/004575
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English (en)
Inventor
Youchun Yan
Frederick William Cain
Ulrike Schmid
Wiro Stam
Jeanet Gerritsen
Original Assignee
Loders Croklaan B.V.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Loders Croklaan B.V. filed Critical Loders Croklaan B.V.
Priority to DE602004011383T priority Critical patent/DE602004011383T2/de
Priority to EP04791612A priority patent/EP1684597B1/fr
Priority to US10/577,327 priority patent/US20070264412A1/en
Priority to JP2006537424A priority patent/JP2007509624A/ja
Publication of WO2005051103A1 publication Critical patent/WO2005051103A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • A23D7/0056—Spread compositions
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/015—Reducing calorie content; Reducing fat content, e.g. "halvarines"
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • This invention relates to a food product, in particular a foodstuff comprising a fat continuous emulsion.
  • Fat continuous emulsions are contained in a number of foodstuffs, including margarines and low fat spreads.
  • Low fat spreads are disclosed in US 4917915, for example.
  • the fat phase is responsible for at least part of the oral properties of the foodstuffs.
  • Certain low fat spreads are marketed for their health properties, including the ability to reduce cholesterol.
  • WO 98/28990 discloses a method of preparing food seasonings, food ingredients and food items using plant sterols and/or stanols together with raised levels of one or more of magnesium, calcium and potassium. Ingestion of the food is said to lead to a decrease in both cholesterol level and blood pressure.
  • Pine needles are the leaves of plants of the Pinaceae family, including the genus Finns. Certain types of pine needles are available in abundant supply and have been used for various purposes. Pine needle extracts have been described as being useful in specific beverages in JP 08107778 A and JP 07059538. Rice cakes containing pine needle extracts are described in JP 01218562 A.
  • High blood pressure (or hypertension) is known to be associated with many medical problems. High blood pressure directly increases the risk of coronary heart disease and stroke. High blood pressure most predominantly occurs in people over 35 years old but environmental and genetic factors and some medical conditions, such as diabetes mellitus, gout or kidney disease can lead to an increased risk of high blood pressure in people of all ages.
  • US 6,329,000 discloses the use of certain pine needle extracts for treating various diseases including myocarditis, angina, arrhythmia, diabetes, senile dementia, sudden deafness and hypertension.
  • the pine needle extracts are obtained by a relatively simple extraction using water and alcohol as solvents.
  • US 5,607,971 discloses the extraction of vasoactive lipids from Pinus ponderosa using methanol, diethyl ether and methylene chloride. The compounds isolated are esterified alkanediols.
  • US 5,690,984 describes a beverage made from pine needles by boiling the needles in water at high pressure in a pressure vessel together with a mixture of other natural products.
  • Pine needles and their extracts may contain isocupressic acids.
  • Isocupressic acids have been described as causing toxicity problems in beef cattle. It has been found that in US 6,329,000, US 5,607,971 and US 5,690,984, a substantial amount of isocupressic acid remains in the extracts.
  • US 5,466,453 teaches a method for improving the taste of a pine extract.
  • US 6,254,858 relates to a hair treatment composition containing, amongst other components, pine juices.
  • US 187,802 describes a disinfecting composition containing maple sugar and extracts of pine needles and juniper berries. The inventors believe that the products will contain substantial amounts of isocupressic acid.
  • CN-A-1102111 describes the preparation of raw pine needle juice.
  • Pine needle extracts have now been found to be useful for incorporation into food products comprising a fat continuous emulsion.
  • a food product comprising a fat continuous emulsion, wherein the emulsion comprises a material comprising one or more organic compounds, said material being obtainable as an extract from pine needles.
  • the extract is preferably an aqueous extract.
  • the food product comprises an aqueous phase and the material is preferably present in the aqueous phase.
  • the material preferably comprises at least 2 components A and B, wherein A is a compound that is obtainable from a mixture of A and B, such as pine needles, by elution from a silica column using 100 % methanol as eluent and B is a compound obtainable from the same silica column using methanol/water mixtures (5-40 % by volume) in a series of subsequent elutions.
  • A is preferably selected from the group consisting of phytosterol, polyphenols, bioflavonoids, tannins, organic acids and their complexes.
  • the material may comprise one or more compounds A and one or more compounds B.
  • the material comprises A (or total A compounds where more than one A compound is present) in an amount of from 5 to 60 wt %, preferably 10 to 50 wt%, most preferably 15 to 40 wt%, and the material comprises B (or total B compounds where more than one B compound is present) in an amount of from 1 to 15 wt %, preferably 2 to I2wt %, most preferably 3 to 10 wt%, based on the weight of the material.
  • the material comprises at least one compound selected from the group consisting of phytosterol, polyphenols, bioflavonoids, tannins, organic acids and their complexes and at least one compound selected from the group consisting of amino acids, peptides, proteins, quercetin, terpenoids, fiavonol glycosides, bifiavones, proanthocyanidins, polyprenols, lignans and minerals.
  • the material preferably contains isocupressic acid compounds in an amount of less than 0.005 wt%, more preferably less than 0.003 wt%, even more preferably less than 0.002 wt% such as less than 0.001 wt%.
  • isocupressic acid compounds and “isocupressic acids” are used synonymously herein and refer to isocupressic acid itself and and preferably related dite ⁇ ene acids found in pine needles and their extracts, such as imbricatoloic acid, agathic acid, dihydroagathic acid and tetrahydroagathic acid.
  • Isocuppressic acids may be in the form of derivatives of these acids, for example, acetylimbricatoloic acid and acetylisocupressic acid.
  • the material of the invention contains isocupressic acid, imbricatoloic acid, agathic acid, dihydroagathic acid, tetrahydroagathic acid, acetylimbricatoloic acid and acetylisocupressic acid in an amount of less than 0.005 wt%, more preferably less than 0.003 wt%, even more preferably less than 0.002 wt% such as less than 0.001 wt%.
  • the material is free of isocupressic acids or substantially free of isocupressic acids (i.e., to the extent that the presence of isocupressic acids cannot be detected by conventional techniques and/or has no effect on the properties of the composition).
  • the level of isocupressic acids can be determined, for example, by GCMS.
  • Pine needles are preferably from species of pine other than Pinus ponderosa. Pine species include Pinus a ⁇ bicaulis, Pinus aristata, Pinus attenuata, Pinus balfouriana, Pinus banksiana, Pinus bungeana, Pinus cembra, Pinus cembroides, Pinus clausa, Pinus contorta, Pinus coulteri, Pinus densiflora, Pinus echinata, Pinus edulis, Pinus elliottii, Pinus engelmannii, Pinus flexilis, Pinus glabra, Pinus heldreichii, Pinus je ⁇ 'eyi, Pinus lambertiana, Pinus longaeva, Pinus massoniana, Pinus monophylla, Pinus monticola, Pinus mugo, Pinus muricata, Pinus nigra, Pinus palustris, Pinus pan'i ⁇ ora
  • the material is from Pinus massoniana, Pinus tabulaeformis or Pinus yuannensis, more preferably, the material is from Pinus massoniana.
  • the material preferably comprises one or more organic compounds, more preferably two or more organic compounds.
  • Organic compounds are compounds that comprise carbon, hydrogen and oxygen atoms and optionally other atoms such as nitrogen, phosphorus and sulphur.
  • Materials of the invention preferably comprise shikimic acid and/or quinic acid.
  • Shikimic acid is preferably present in the materials of the invention in an amount by weight of the material of at least 10 %, preferably at least 12 %, more preferably at least 15 %, such as at least 16 %, at least 17 %, at least 18 %, at least 19 % or at least 20 %.
  • the upper limit for the amount of shildmic acid is typically no more than 50 %, more preferably no more than 40 %, such as no more than 30 %, or no more than 25 %, again by weight of the material.
  • the shikimic acid may be present as a salt or other derivative, such as an acetyl ester.
  • Quinic acid (typically as D-quinic acid) is preferably present in the materials of the invention in an amount by weight of the material of at least 5 %, preferably at least 6 %, more preferably at least 7 %, such as at least 8 %, at least 9 %, at least 10 %, at least 12 % or at least 15 %.
  • the upper limit for the amount of quinic acid is typically
  • the quinic acid may be present as a salt or other derivative, such as an acetyl ester.
  • Specific preferred materials of the invention comprise shikimic acid and quinic acid in the amounts specified in the preceding two paragraphs.
  • An example of such a material comprises at least 10 % by weight shikimic acid and at least 5 % by weight quinic acid, such as 10 % to 30 % shikimic acid and 5 % to 20 % quinic acid.
  • Materials of the invention may further comprise low molecular weight sugars, preferably sugars having a molecular weight below 1000 Daltons.
  • Preferred low molecular weight sugars are monosaccharide units and include glucose, fructose and inositol.
  • the amount of low molecular weight sugars is preferably from 15 % to 50 % by weight, such as 20 % to 40 %, or 20 % to 35 % by weight of the material.
  • the material is preferably obtainable by a process which comprises the following steps: treating pine needles with a solvent selected from water, organic solvents and mixtures thereof (preferably water), preferably at an elevated temperature of from 40 °C to 110 °C 5 to form a first extract; removing isocupressic acid compounds from the first extract, preferably by treatment with an ion exchange resin and/or activated carbon (preferably whilst the first extract is in aqueous solution, more preferably at an elevated temperature); and optionally, filtering and concentrating the treated extract to obtain the material as a powder or a concentrate.
  • a solvent selected from water, organic solvents and mixtures thereof (preferably water), preferably at an elevated temperature of from 40 °C to 110 °C 5 to form a first extract
  • isocupressic acid compounds from the first extract, preferably by treatment with an ion exchange resin and/or activated carbon (preferably whilst the first extract is in aqueous solution, more preferably at an elevated temperature)
  • filtering and concentrating the treated extract
  • the pine needles are pretreated with a non-polar solvent (e.g, an alkane having from 4 to 10 carbon atoms, such as hexane), more preferably at a temperature of from 40 °C to 90 °C.
  • a non-polar solvent e.g, an alkane having from 4 to 10 carbon atoms, such as hexane
  • This pretreatment typically removes at least a part of the isocupressic acids.
  • the food product can consist of, or consist essentially of, the fat continuous emulsion (e.g., in the case of certain margarines or low fat spreads).
  • the fat continuous emulsion can constitute all of the food product.
  • the food product can contain the fat continuous emulsion together with one or more other food ingredients or additives.
  • the fat continuous emulsion preferably has a fat content of from 0.5 to 99.5 wt%, preferably 20 to 85 wt%, most preferably 30 to 80 wt%, based on the weight of the food product.
  • Water is preferably present in the food product in an amount of from 0.5 to 99.5 wt%, more preferably 10 wr% to 50 wt%.
  • the food product thus preferably comprises an aqueous phase and a fat phase.
  • the solid fat content of the fat in the fat continuous emulsion can conveniently be determined by measuring the NMR N-value as described in Fette, Seifen, Anstrichsch, 80 (1978), 180-186, which indicates the amount of fat present in the solid state expressed in percentage of the weight of the fat.
  • Non-stabilised means that the N-value is measured after first melting the fat above 80° C, whereupon the melt is cooled to 0° C and kept at 0° C for 30 minutes, then the fat is heated to the measurement temperature and kept at that temperature for 30 minutes, whereupon the N-value is measured.
  • One embodiment of the invention is a food product comprising fat and water and having a fat content of from 0.5 to 99.5 wt %, wherein the fat phase comprises at least two components (D) and (E), (D) having an N20>20 and (E) having a content of mono- and di-unsaturated fatty acid residues of at least 25 wt%.
  • Component (D) is preferably selected from the group consisting of palm fractions, interesterified hardened palm oil and hardened palm kernel oil and fractions thereof, interesterified mixtures of liquid oils and hardened liquid oils, interesterified fractions of palm kernel oil and palm oil, particularly palm kernel stearine and palm oil stearine, and fractions thereof, and fats containing at least 20 wt % of SUS triglycerides.
  • (E) has a content of mono- and di-unsaturated fatty acid residues of from 55 to 95 wt% and examples of component (E) include oils selected from the group consisting of sunflower oil, high oleic sunflower oil, rape seed oil, high oleic rape seed oil, palm oil olein, corn oil, soybean oil and high oleic soybean oil.
  • the weight ratio of (D) to (E) is preferably from 10:1 to 1:20, more preferably from 1:1 to 1:15, even more preferably from 1 :4 to 1:10.
  • the food products of the invention are essentially free of trans fatty acids (which are carboxylic acids containing from 12 to 24 carbon atoms and having one carbon-carbon double bond) i.e., they contain trans fatty acids in an amount of less than 1% by weight, preferably less than 0.5% by weight, more preferably less than 0.1% by weight, such as less than 0.05% or less than 0.01% by weight.
  • trans fatty acids which are carboxylic acids containing from 12 to 24 carbon atoms and having one carbon-carbon double bond
  • the food product preferably contains the material in an amount of from 0.01wt% to 20wt% (e.g., 0.01wt% to 1 wt%), more preferably from 0.05wt% to 15wt% (e.g., 0.05wt% to 1 wt%), even more preferably from 0.1wt% to 12wt% (e.g., 0.1wt% to 1 wt%), based on the total weight of the food product and on the weight of the dry material.
  • 0.01wt% to 20wt% e.g., 0.01wt% to 1 wt%
  • 0.05wt% to 15wt% e.g., 0.05wt% to 1 wt%
  • 0.1wt% to 12wt% e.g., 0.1wt% to 1 wt%
  • the food product of the invention preferably has one or more of the following properties compared to a corresponding product that does not contain the material: increased hardness, improved texture, increased aeration, improved spreadability, improved oral properties, improved mouthfeel, improved flavour impact, better colour, improved viscosity, increased ease of processing and improved health properties.
  • the properties are improved compared to an otherwise identical food product that does not contain the material.
  • Preferred properties that are improved according to the invention are oral properties and/or visual appearance, in particular increased similarity to butter in terms of oral properties and/or visual appearance.
  • Increased hardness of the food product is a particularly preferred advantage of the invention.
  • the increased hardness is, for example, evident when the product is spread onto a substrate with a knife.
  • the material of the invention has therapeutic activity.
  • therapeutic activity in this context means usefulness in the treatment, inhibition or prevention of diseases or disorders. Diseases and disorders include, but are not limited to, high blood pressure (hypertension).
  • the invention provides a food product of the invention, for use to lower blood pressure in mammals, particularly humans.
  • the invention may involve one or more of the following effects: lowering blood pressure; lowering systolic and/or diastolic blood pressure; reducing heart rate; reducing sympathetic nerve activity; reducing the chance of coronary heart disease; reducing the chance of aneurisms; reducing the chance of strokes; improving blood circulation; improving the cardiovascular system; improving blood vessel health; reducing stress on smooth muscle tissue; reducing the chance of chest pains; providing part of a healthy lifestyle; improving the chance of healthy circulation; reducing the effect of aging on the blood vessels; reducing cardiac stress; and improving recovery time after exercising.
  • the invention also involves a method of lowering blood pressure (and/or treating hypertension) in a mammal which comprises the provision of an effective amount of a food product of the invention.
  • the invention further contemplates the use of a food product of the invention in the manufacture of a composition for treating and/or preventing hypertension.
  • Preferred food products of the invention are margarines, low fat spreads, bakery spreads and cooking spreads. These products may be packaged and labelled for sale and are typically stored at low temperature (e.g., below 15°C).
  • Preferred packaging includes containers with lids, preferably of plastics material and of a size sufficient to hold from 25 g to 1 kg of the food product.
  • Margarines and spreads can be made by using conventional techniques for the preparation of margarines, low fat spreads or very low fat spreads (less than 40wt% fat) (as disclosed for example in EP 089082, the contents of which are incorporated herein by reference) .
  • a spread preferably has a continuous fat phase to give it suitable spreadability and to prevent microbiological deterioration. It should not release moisture when it is being spread. Furthermore, a spread should preferably be spreadable at refrigerator temperature (5°C), be stable at room temperature (20°C), but destabilize and release its flavour in the mouth.
  • the margarine or spread is a dispersion having a plastified continuous fat phase and a dispersed aqueous phase.
  • continuous fat phase is meant to include the oil present in the liquid state and forming a continuous phase as well as the solid fat particles contained in the liquid oil that have been phase-separated from the liquid oil by crystallization of fat by the plastification treatment.
  • the "continuous fat phase” does not, however, include any fat contained in the dispersed aqueous phase, as occurs e.g., in a product having a so-called oil-in-water-in-oil structure.
  • the aqueous phase may comprise, apart from water, a gelling agent and, optionally, a thickener and/or one or more other ingredients that are commonly incorporated in margarines and spreads, e.g. flavouring agents, colouring agents, emulsifiers, salt, preservative and acid.
  • additives may be contained in the fat phase composition.
  • the fat phase composition may comprise a blend of triglycerides supplemented with one or more emulsifiers and/or colouring agents.
  • the aqueous phase composition may include some fat, but preferably the fat content of the aqueous phase composition is not higher than about 10 wt.%. It is particularly preferred that the aqueous phase composition comprises essentially no fat.
  • oil and fat are used interchangeably. They are meant to include triglycerides such as soyabean oil, sunflower oil, palm oil, fish oil, rapeseed oil, coconut oil, chemically and/or physically modified products such as hydrogenated, fractionated and/or interesterified triglyceride mixtures and mixtures of two or more thereof, as well as edible substances that are physically similar to triglycerides such as waxes, e.g. jojoba oil, and poly fatty acid esters of mono- or disaccharides, and that can be used as replacement for or in admixture with triglycerides.
  • the fat contained in the present spreads consists essentially of triglycerides.
  • the aqueous phase and/or the fat phase can suitably include emulsifiers.
  • the amount and kind of emulsifier included are not critical. It is preferred to incorporate emulsifiers of the type and quantity as are commonly used in spreads.
  • emulsifiers of the type and quantity as are commonly used in spreads.
  • mixtures of mono- and diglycerides derived from natural, partially hydrogenated or ftilly hardened sunflower oil can suitably be employed, using an amount of about 0.2 to about 0.5 wt.%, calculated on the total weight of aqueous phase and fat phase.
  • other oil-compatible emulsifiers can be used. Mixtures of such emulsifiers with mono- and/or diglycerides can also be suitable as emulsifier.
  • the average droplet size of the dispersed aqueous phase is such that a satisfactory flavour release in the mouth can be obtained, while the product can have an adequate microbiological stability.
  • Droplet sizes may be between about 3 ⁇ m and about 60 ⁇ m, but it may be larger or smaller than that.
  • the average droplet size is the volume weighted mean of the droplet size distribution. It can be determined with NMR following the procedure as described in J. Colloid and Interface Science (1972), 10, 206 and (1983), 93, 521.
  • the average droplet size of the present spreads can be varied easily, by adjusting the conditions during the preparation.
  • the present spreads can suitably be used e.g. on bread as butter substitutes. However, they can also be suitable for use as complete spread on their own, for example when containing a cheese or vegetable or fruit flavours or pieces.
  • Figure 1 shows the dose dependent contraction of rat aorta caused by phenylephrine and the inhibition of this effect by a pine needle extract of the invention.
  • Thoracic aortas were obtained from spontaneous hypertensive rats (SHR).
  • the thoracic aorta is cut into rings of 4 to 6 mm in length and each ring is connected to a tension transducer in a thermostatically controlled and oxygenated organ bath containing modified Krebs-Henselheit buffer.
  • the contractions of rings of aorta are recorded continuously under isotonic conditions.
  • a single dose of l ⁇ M phenylephrine was given to sensitise the tissue, followed by washout.
  • two cumulative dose response curves of phenylephrine were generated. The first dose response curve was obtained in the absence of an extract and served as a control curve.
  • the following is an example of a spread according to the invention.
  • the spread can be prepared according to the procedure described in Example 14 of WO 97/18320.
  • Hymono 7804 emulsifier 0.3 %
  • the first extract (Extract 1) is a comparative example containing isocupressic acids.
  • the second example (Extract 2) is a purified form of the first extract and is an example of a material according to the invention.
  • Extract 1 was obtained as follows:
  • the pine needle extract (Extract 1) was obtained by removing water using a rotary evaporator.
  • Extract 2 was obtained by further treating Extract 1 as follows: • 200 g pine needle extract obtained above as Extract 2 (containing ⁇ 5-10% water) was mixed with 1.2 1 demineralised water. This was allowed to stand in a water bath at 70 °C for half and hour to dissolve. • The mixture was transported to a reaction vessel and stirred for 15 minutes at 70 °C. • 40 g resin (Dowex 50 W) was added and stirring was continued for three hours at 50 °C, the mixture was then filtered. After the filtration, this step (i.e., addition of resin, stirring and filtering) was repeated. • 0.8g of Norit SA4 active carbon was added. • The resulting mixture was stirred for 1 hour while keeping the temperature at 85 °C. • The resulting mixture was filtered 3 times through a B ⁇ chner filter (54; 0185mm). • Water was evaporated from the filtrate using a rotary evaporator to obtain Extract 2.
  • ICA isocupressic acid
  • the sample is extracted with 50 mL methylene chloride for about three hours by means of a method based on Soxhlet extraction. After extraction, the mehylene chloride is removed via rotary evaporation. After this step, heptadecanoic acid is added as an internal standard. This component is used to be able to quantify in the end.
  • the samples are then dissolved in a little methylene chloride and put on a SPE column containing 500 mg of aminopropyl sorbent, which has been conditioned with the appropriate solvents beforehand. After the sample has been put on the SPE column the possible present "neutral" components are eluted with a solvent containing 9:1 by volume diether ether: methanol.
  • the acids are eluted with the same solvent but containing an additional 1% of acetic acid.
  • the sample is derivatized by means of 2 M diazomethane in ether (making methyl esters of the carboxylic acid groups) and by using MSTFA (N-methyl-N-trimethylsilyltrifluoroacetamide) for silylating any free hydroxyl groups left.
  • MSTFA N-methyl-N-trimethylsilyltrifluoroacetamide
  • the GC-MS uses a 30 m CP-Sil 5 column (DB-1) with an internal diameter of 0.25 mm to separate the components. Temperature programming is used: 100 C, 1 minute hold ramped to 200 C at 40 °C / min after which the temperature is ramped to 250 °C at 2 °C /min.
  • Splitless injection is used and the temperature of the injector is kept constant at 250 °C.
  • MS transfer line is also kept constant at 250 °C.
  • the MS detector was set to El mode with an ionization energy of 70 eV.
  • the mass range collected was from 50 to 550 Da using an electron multiplier voltage of 1250 V.
  • Table 1 shows the effect of pine needle extract on - the median effective concentration (EC5 0 ) of phenylephrine and the difference between DRC1 and DRC2 - maximal effect (E ma ⁇ ) relative to phenylephrine; the lower the value the more effective the extract
  • Isolated aorta rings from spontaneously hypertensive rats were used as a model for testing vasoactive effects.
  • Thoracic aortas were obtained from the SHR rats.
  • the thoracic aorta was cut into rings of 4 to 6 mm in length and each ring was then connected to a tension transducer in a thermostatically controlled and carbogentaed organ bath containing modified Krebs-Henseleit buffer.
  • the contractions of rings of aorta were recorded continuously under isotonic conditions. After equilibrating the tissues, a single dose of l ⁇ M phenylephrine was given to sensitise the tissue, followed by washout.
  • Phenylephrine is an ⁇ -adenergic agonist, and is used in this experiment to induce contraction of the aorta rings.
  • DRC1 and DRC2 two cumulative dose response curves (DRC1 and DRC2) of phenylephrine were generated.
  • DRC1 was obtained in the absence of an extract and served as a control curve, while DRC2 was obtained after incubation with 50 ⁇ g/mL pine needle extract. After thorough washing the tissues were incubated with the pine needle extract for 5 minutes. Following this incubation period, a second dose response curve was obtained in the presence of a concentrated form of the extract. The data were analysed taking - the median effective concentration (EC50) - maximal effect (E max ) relative to phenylephrine
  • ICA family consists of dihydroagathic acid, imbricatoloic acid, isocupressic acid, agathic acid, acetylimbricatoloic acid and acetylisocupressic acid.
  • Low molecular weight sugars are monosaccharide units and include glucose, fructose and inositol structures.
  • Extract 1 After incubation with Extract 1 the contraction of the rat aorta by phenylephrine is clearly inhibited (Emax 54). Extract 2 shows after removal of isocupressic acids by Norit treatment and ion exchange still activity (Emax 79) similar to extracts 5, 6, and 7 which are high in isocupressic acids.
  • the process line was set up in an AAC configuration.
  • the A-unit is a scraped surface heat exchanger and the C-unit is a pin mill (kneader).
  • the volume of the C-unit was reduced to 1/3 and the numbers of the pins on the shaft of the kneader was reduced from 17 to 5.
  • the temperatures of the product inlet, outlet and the cooling medium were registered. .
  • Preparation of the water phase For preparation and pasteurizing of the water phase the mixing, dispersing and homogenizing device was used. This device had a 25 litre thermally controlled vessel with a scraped anchor agitator. During dissolving/dispersing of the dry materials of the water phase in the water, the mixture is circulated continuously and temperature of the water phase is monitored in-line in the mixing zone of the colloid mill. The mixture was pasteurized at 70 °C during 10 minutes. Afterwards the water phase was cooled down till approximately 55 D C without mixing. Preparation of the fat phase During stirring, all ingredients of the fat phase were molten under nitrogen atmosphere, and heated till about 80 °C. Afterwards, the fat phase was cooled down under continuous stirring till 55 °C.
  • Emulsification The water phase was added slowly to the fat phase under intensive stirring and emulsified to a water-in-oil emulsion. During emulsification the emulsion was tempered at 55 °C for at least 30 minutes. Processing A 30 kg-batch size was employed. The mix was stirred for 15 minutes before pumping. After pumping, the line was allowed to run for 15 minutes before any collection of product. During processing, the mass flow was fixed at approximately 50 kg/h. At the indicated measuring points the temperature was measured. When a stable situation was reached, 15 tubs were filled with approximately 125g margarine. The following process parameters (temperatures in °C) were recorded:
  • the results of the product evaluation are given in table below.
  • the spreads containing pine needle extract had a higher c-value for hardness than standard spreads. All samples spread easily with no apparent water loss.
  • the spreads of the invention had, in addition to increased hardness, good spreadability, good structure, good tailing and good sticking to the knife.

Abstract

Un produit alimentaire comprend une émulsion grasse continue, ladite émulsion comprenant une matière constituée d'un ou plusieurs composés organiques, ledit matériau pouvant être obtenu en tant qu'extrait d'aiguilles de pin.
PCT/GB2004/004575 2003-10-30 2004-10-29 Produit alimentaire comprenant un extrait a base d'aiguilles de pin WO2005051103A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
DE602004011383T DE602004011383T2 (de) 2003-10-30 2004-10-29 Nahrungsmittel mit kiefernnadelextrakt
EP04791612A EP1684597B1 (fr) 2003-10-30 2004-10-29 Produit alimentaire comprenant un extrait a base d'aiguilles de pin
US10/577,327 US20070264412A1 (en) 2003-10-30 2004-10-29 Food Product Comprising an Extract From Pine Needles
JP2006537424A JP2007509624A (ja) 2003-10-30 2004-10-29 松葉からの抽出物を含む食品

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP03256869 2003-10-30
EP03256869.3 2003-10-30

Publications (1)

Publication Number Publication Date
WO2005051103A1 true WO2005051103A1 (fr) 2005-06-09

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EP (1) EP1684597B1 (fr)
JP (1) JP2007509624A (fr)
CN (1) CN1889857A (fr)
AT (1) ATE383779T1 (fr)
DE (1) DE602004011383T2 (fr)
ES (1) ES2300838T3 (fr)
WO (1) WO2005051103A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1889546A1 (fr) * 2006-08-17 2008-02-20 Unilever N.V. Mélange alimentaire particulaire contenant de la graisse
WO2011159144A1 (fr) 2010-06-16 2011-12-22 Malaysian Palm Oil Board Compositions contenant de l'acide shikimique obtenues à partir de matériaux à base de palmier à huile et leur procédé de fabrication

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009059890A1 (fr) * 2007-11-06 2009-05-14 Unilever Nv Produit alimentaire
WO2011019654A1 (fr) * 2009-08-10 2011-02-17 Stokely-Van Camp, Inc. Procédé pour mettre un flavonoïde en suspension dans une boisson
US8318233B2 (en) * 2010-03-26 2012-11-27 Corn Products Development Inc Emulsions useful in beverages
CN102807458A (zh) * 2012-06-08 2012-12-05 上海慧塔实业有限公司 一种蓝莓种植的专用制剂及其制备工艺
CN108936466A (zh) * 2017-05-19 2018-12-07 吉林农业大学 一种火炬树芽食材
KR102020300B1 (ko) * 2019-06-14 2019-09-10 박진옥 우지를 이용한 버터 대용품 및 이의 제조 방법

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1102111A (zh) * 1993-10-27 1995-05-03 董雍年 松针原汁的提取方法
US5466453A (en) * 1992-04-02 1995-11-14 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Method for improving the taste of pine extract, and orally administrable product obtained thereby
US6190680B1 (en) * 1998-04-01 2001-02-20 The Nisshin Oil Mills, Ltd. Oily composition and process for producing the same
KR20010017516A (ko) * 1999-08-12 2001-03-05 박인배 새로운 멜라닌 생합성 저해제
EP1129711A2 (fr) * 2000-02-24 2001-09-05 Unilever N.V. L'acide pinolénique contre le diabète
KR20010091281A (ko) * 2000-03-14 2001-10-23 정찬봉 찐빵 제조방법
US6329000B1 (en) * 1997-01-27 2001-12-11 Ling Ji Extract of pine needle and the use thereof
WO2004064757A2 (fr) * 2003-01-23 2004-08-05 Shire Laboratories, Inc. Agents facilitant l'absorption

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US187802A (en) * 1877-02-27 Improvement in disinfecting compounds
FI89448C (fi) * 1986-03-06 1993-10-11 Unilever Nv Foerfarande foer framstaellning av en bredning
US5494667A (en) * 1992-06-04 1996-02-27 Kabushiki Kaisha Hayahibara Topically applied hair restorer containing pine extract
CA2173545C (fr) * 1995-04-07 2004-06-29 Kalyana Sundram Augmentation du taux de lphd et du rapport lphd/lpbd dans le serum humain par equilibre des acides gras alimentaires satures et non satures
US5607971A (en) * 1995-06-19 1997-03-04 University Of Iowa Research Foundation Esterified vasoactive lipids for increasing perfusion pressure of the caruncular arterial bed in mammals
JPH0947267A (ja) * 1995-08-10 1997-02-18 Jun Jen Lim 松葉エキス飲料の製造方法
KR100258419B1 (ko) * 1997-11-03 2000-07-01 한승희 탈모를예방하는모발용화장조성물및그조성물의제조방법

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5466453A (en) * 1992-04-02 1995-11-14 Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo Method for improving the taste of pine extract, and orally administrable product obtained thereby
CN1102111A (zh) * 1993-10-27 1995-05-03 董雍年 松针原汁的提取方法
US6329000B1 (en) * 1997-01-27 2001-12-11 Ling Ji Extract of pine needle and the use thereof
US6190680B1 (en) * 1998-04-01 2001-02-20 The Nisshin Oil Mills, Ltd. Oily composition and process for producing the same
KR20010017516A (ko) * 1999-08-12 2001-03-05 박인배 새로운 멜라닌 생합성 저해제
EP1129711A2 (fr) * 2000-02-24 2001-09-05 Unilever N.V. L'acide pinolénique contre le diabète
KR20010091281A (ko) * 2000-03-14 2001-10-23 정찬봉 찐빵 제조방법
WO2004064757A2 (fr) * 2003-01-23 2004-08-05 Shire Laboratories, Inc. Agents facilitant l'absorption

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
DATABASE BIOSIS BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; 1980, LINDNER W, GRILL D: "Acids in conifer needles", XP002311085, Database accession no. 198069060322 *
DATABASE WPI Derwent World Patents Index; AN 1997-272844, XP002272810, DONG Y, WANG S, ZHANG R: "Method for extracting raw pine needle juice" *
DATABASE WPI Derwent World Patents Index; AN 2002-203307, XP002272811, JEONG CB: "Production of steamed bread" *
DATABASE WPI Week 2001, Derwent World Patents Index; AN 2001-495315, XP002311086, LEE HG, LEE SJ, LEE YH, PARK SY: "Novel melanin biosynthesis inhibitor" *
LEE Y-H ET AL: "THE CHOLESTEROL-LOWERING EFFECTS OF THE EXTRACT FROM PINUS STOBUS IN CHICKENS", HANGUG NYENNYAN SIGRYAN HAGHOI JI - JOURNAL OF THE KOREAN SOCIETY OF FOOD AND NUTRITION, PUSAN, KR, vol. 25, no. 2, 1996, pages 188 - 192, XP001026939, ISSN: 0253-3154 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1889546A1 (fr) * 2006-08-17 2008-02-20 Unilever N.V. Mélange alimentaire particulaire contenant de la graisse
WO2011159144A1 (fr) 2010-06-16 2011-12-22 Malaysian Palm Oil Board Compositions contenant de l'acide shikimique obtenues à partir de matériaux à base de palmier à huile et leur procédé de fabrication
EP2582654A1 (fr) * 2010-06-16 2013-04-24 Malaysian Palm Oil Board Compositions contenant de l'acide shikimique obtenues à partir de matériaux à base de palmier à huile et leur procédé de fabrication
EP2582654A4 (fr) * 2010-06-16 2015-12-16 Malaysian Palm Oil Board Compositions contenant de l'acide shikimique obtenues à partir de matériaux à base de palmier à huile et leur procédé de fabrication
US9963415B2 (en) 2010-06-16 2018-05-08 Malaysian Palm Oil Board Compositions comprising shikimic acid obtained from oil palm based materials and method of producing thereof
US10308583B2 (en) 2010-06-16 2019-06-04 Malaysian Palm Oil Board Compositions comprising shikimic acid obtained from oil palm-based materials

Also Published As

Publication number Publication date
EP1684597B1 (fr) 2008-01-16
US20070264412A1 (en) 2007-11-15
ES2300838T3 (es) 2008-06-16
DE602004011383D1 (de) 2008-03-06
CN1889857A (zh) 2007-01-03
DE602004011383T2 (de) 2008-08-07
JP2007509624A (ja) 2007-04-19
ATE383779T1 (de) 2008-02-15
EP1684597A1 (fr) 2006-08-02

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